5 Questions Freelancers Need to Ask Before Taking a Leave of Absence

There’s a running joke among entrepreneurs that we are the only people who will work 80 hours a week for ourselves to avoid working 40 hours a week for someone else. This doesn’t always have to be true, but for many freelancers and small business owners, it hits a little close to home.

When you work for yourself, you theoretically get freedom to decide your own schedule. But the downside of not having a set time you need to be at the office is that it’s sometimes hard to stop working. And thinking about getting more work. And worrying about not having enough work. On and on and on. But what’s the point of being your own boss if you never get a day off?

Taking time away from your own business can seem terrifyingly impossible. You may have subcontractors or employees, but there’s no substitute for you, the CEO and project lead. (And marketing department and sales team and accountant…) That’s just reality, and I’m not going to pretend otherwise. But if you’re planning for vacation, parental leave, recovery time from medical care, or just some much-needed down time, here are five questions to ask yourself.

Why am I taking time off?

You don’t need to justify taking a break to anyone, but it helps to understand your own motivation so you can plan accordingly. I took three months off from paid client work at the beginning of 2019 to learn email marketing strategy and finish a few pro bono web projects for communities that are important to me. (It was also cold, flu, and snow season for my minion so a lighter workload made sense.) Knowing what I hoped to gain during that break in producing income helped me stay focused on my professional development and community projects. If you’re planning parental leave, remember you’re taking that time to bond with your family and adjust to a new reality. If you’re going on vacation, are you looking for rest, inspiration, or both? Remind yourself of those reasons whenever you feel tempted to cut your break short.

Who will do my work when I’m gone?

Ideally, you’ll be able to wrap any ongoing projects or get them to a logical pause point before your vacation or leave begins. But that doesn’t always work out. If your work tends to be ongoing, like virtual assisting or social media management, rather than project-based, you may want to consider building relationships with a few good pinch hitters who do the same kind of work. Contract with them to take over specific tasks while you’re out. You may also be able to work ahead and schedule content to run automatically in your absence.

What will I do with new business inquiries?

I think the hardest part about taking time off as a freelancer is the opportunity cost of telling people you’re not open for business. In my three-month sabbatical, not only was I not making money, I was also missing out on bookings because I wasn’t available when they asked. But there are a few ways to spin a leave of absence in your favor.

First, it never hurts to ask if someone is willing to wait until you’re back to work. Your services shouldn’t be an impulse purchase, and few people are in as big of a hurry as they think they are. If you’ve been smart about your marketing, potential clients will want to specifically work with you over any other [whatever it is you do]. Reward that motivation with a small discount or added value to start later. (Sign a contract and get a deposit, of course.)

If someone can’t wait, tap into your professional network and refer them to someone qualified and trustworthy. You’ll have made yourself helpful to both the client and your colleague, and that sets a good precedent for receiving referrals in return. I wouldn’t ask for a referral fee outright (unless it’s already standard in your industry, such as in real estate); think of it instead as banking goodwill and connections for yourself later.

How connected will I stay during leave?

Refer back to your reasons for taking leave in the first place to help you decide how in touch you want to be. For those facing the imminent arrival of a tiny human in their life, I highly recommend disconnecting from your business email and setting responses on autopilot, at least for the first month or two. You might not know what planet you’re on, so you probably shouldn’t be answering emails. If you’re going to be out for more than a few weeks, don’t forget to look at your overhead expenses. Can you pause or cancel subscription services you won’t need for awhile? See if you can postpone purchases or expenditures until after you get back.

If you’re going on vacation or taking medical leave, establish boundaries that feel comfortable for you and communicate those to your clients and vendors. Maybe you’ll check email once a day but only respond to urgent matters on Monday and Friday. Maybe you check in with select clients once a week about specific projects or tasks. I wouldn’t recommend letting clients decide what constitutes “urgent” matters that need your attention.

How will I get back to work?

Whether you’re gone for two days or two months, give yourself some time to get back up to speed when you return. Don’t panic if things are slow at first. You could start working a few days before your announced “back in office;” I suggest taking care of deferred administrative tasks like billing, bookkeeping, ordering supplies and inventory, or creating marketing content before jumping back in with clients. If you’ve been turning away new business during your break, be prepared to spend some time refilling your pipeline. You might want to schedule some networking opportunities when you’re back in the saddle. And definitely make sure ahead of time that your cash flow and savings can tolerate a slowdown in income.

There are many good reasons to take time off from your freelance work or small business: family, rest, travel, education, inspiration. In fact, many of those reasons are probably the same reasons you started working for yourself in the first place. Don’t let fear stop you from taking time off. With proper planning, you’ll come back ready to grow and create better than ever.

Jennifer Duann Fultz

Welcome to a space of creativity, honesty, and plenty of Asian auntie attitude. Here you’ll find reflections on life, glimpses of my novel (estimated publication date 2074), and hard-ass advice for creative freelancers. If you’re looking for fluffy Instagram inspiration about never working a day in your life, you should probably leave.